CA1268594A - Process for the preparation of optically active polyolefins - Google Patents

Process for the preparation of optically active polyolefins

Info

Publication number: CA1268594A
Authority: CA; Canada
Prior art keywords: optically active; transition metal; aluminoxane; metal compound; poly
Prior art date: 1985-03-13
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related

Application number

CA000503755A

Other languages

English (en)

French (fr)

Inventor

Walter Kaminsky

Stefan Niedoba

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1985-03-13

Filing date

1986-03-11

Publication date

1990-05-01

1986-03-11 Application filed by Hoechst AG filed Critical Hoechst AG

1990-05-01 Application granted granted Critical

1990-05-01 Publication of CA1268594A publication Critical patent/CA1268594A/en

2007-05-01 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 19
230000008569 process Effects 0.000 title claims abstract description 16
229920000098 polyolefin Polymers 0.000 title claims abstract description 11
238000002360 preparation method Methods 0.000 title claims abstract description 11
239000003054 catalyst Substances 0.000 claims abstract description 17
150000003623 transition metal compounds Chemical class 0.000 claims abstract description 12
229910052782 aluminium Inorganic materials 0.000 claims abstract description 6
150000001875 compounds Chemical class 0.000 claims abstract description 6
150000001336 alkenes Chemical class 0.000 claims abstract description 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract description 3
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims abstract description 3
230000000379 polymerizing effect Effects 0.000 claims abstract description 3
-1 hydrocarbon radical Chemical class 0.000 claims description 23
238000006116 polymerization reaction Methods 0.000 claims description 15
239000004215 Carbon black (E152) Substances 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
CPOFMOWDMVWCLF-UHFFFAOYSA-N methyl(oxo)alumane Chemical compound C[Al]=O CPOFMOWDMVWCLF-UHFFFAOYSA-N 0.000 claims description 6
RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 5
229910052719 titanium Inorganic materials 0.000 claims description 5
239000010936 titanium Substances 0.000 claims description 5
229910052723 transition metal Inorganic materials 0.000 claims description 5
150000003624 transition metals Chemical class 0.000 claims description 5
239000000178 monomer Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 2
ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 2
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical group C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 2
239000007788 liquid Substances 0.000 claims description 2
150000003755 zirconium compounds Chemical class 0.000 claims description 2
YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims 1
239000004743 Polypropylene Substances 0.000 description 13
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
229920001155 polypropylene Polymers 0.000 description 10
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
229920000642 polymer Polymers 0.000 description 7
229910052726 zirconium Inorganic materials 0.000 description 7
NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 6
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 4
QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 4
235000010210 aluminium Nutrition 0.000 description 4
230000000694 effects Effects 0.000 description 4
229940095050 propylene Drugs 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
239000000203 mixture Substances 0.000 description 2
238000006384 oligomerization reaction Methods 0.000 description 2
229920001083 polybutene Polymers 0.000 description 2
SYTBZMRGLBWNTM-SNVBAGLBSA-N (R)-flurbiprofen Chemical compound FC1=CC([C@H](C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-SNVBAGLBSA-N 0.000 description 1
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
239000005062 Polybutadiene Substances 0.000 description 1
239000012190 activator Substances 0.000 description 1
230000032683 aging Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
229910000329 aluminium sulfate Inorganic materials 0.000 description 1
DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
238000007664 blowing Methods 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229910052804 chromium Inorganic materials 0.000 description 1
239000011651 chromium Substances 0.000 description 1
125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000000835 fiber Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229920001519 homopolymer Polymers 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
229920002857 polybutadiene Polymers 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000004416 thermosoftening plastic Substances 0.000 description 1
150000003609 titanium compounds Chemical class 0.000 description 1
WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
229910052721 tungsten Inorganic materials 0.000 description 1
239000010937 tungsten Substances 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
229910052845 zircon Inorganic materials 0.000 description 1
GFQYVLUOOAAOGM-UHFFFAOYSA-N zirconium(iv) silicate Chemical compound [Zr+4].[O-][Si]([O-])([O-])[O-] GFQYVLUOOAAOGM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F10/00—Homopolymers and copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/65912—Component covered by group C08F4/64 containing a transition metal-carbon bond in combination with an organoaluminium compound
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/60—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides together with refractory metals, iron group metals, platinum group metals, manganese, rhenium technetium or compounds thereof
- C08F4/62—Refractory metals or compounds thereof
- C08F4/64—Titanium, zirconium, hafnium or compounds thereof
- C08F4/659—Component covered by group C08F4/64 containing a transition metal-carbon bond
- C08F4/6592—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring
- C08F4/65922—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not
- C08F4/65927—Component covered by group C08F4/64 containing a transition metal-carbon bond containing at least one cyclopentadienyl ring, condensed or not, e.g. an indenyl or a fluorenyl ring containing at least two cyclopentadienyl rings, fused or not two cyclopentadienyl rings being mutually bridged
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S526/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S526/943—Polymerization with metallocene catalysts

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)

CA000503755A 1985-03-13 1986-03-11 Process for the preparation of optically active polyolefins Expired - Fee Related CA1268594A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19853508887 DE3508887A1 (de)	1985-03-13	1985-03-13	Verfahren zur herstellung von optisch aktiven polyolefinen
DEP3508887.7		1985-03-13

Publications (1)

Publication Number	Publication Date
CA1268594A true CA1268594A (en)	1990-05-01

Family

ID=6265013

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000503755A Expired - Fee Related CA1268594A (en)	1985-03-13	1986-03-11	Process for the preparation of optically active polyolefins

Country Status (5)

Country	Link
US (1)	US4933403A (de)
EP (1)	EP0197319B1 (de)
JP (1)	JPS61264010A (de)
CA (1)	CA1268594A (de)
DE (2)	DE3508887A1 (de)

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1985
- 1985-03-13 DE DE19853508887 patent/DE3508887A1/de not_active Withdrawn
1986
- 1986-03-07 DE DE8686103086T patent/DE3666439D1/de not_active Expired
- 1986-03-07 EP EP86103086A patent/EP0197319B1/de not_active Expired
- 1986-03-11 CA CA000503755A patent/CA1268594A/en not_active Expired - Fee Related
- 1986-03-11 US US06/838,678 patent/US4933403A/en not_active Expired - Lifetime
- 1986-03-12 JP JP61052756A patent/JPS61264010A/ja active Pending

Also Published As

Publication number	Publication date
JPS61264010A (ja)	1986-11-21
DE3666439D1 (en)	1989-11-23
EP0197319B1 (de)	1989-10-18
EP0197319A3 (en)	1987-09-30
EP0197319A2 (de)	1986-10-15
US4933403A (en)	1990-06-12
DE3508887A1 (de)	1986-09-25

Legal Events

Date	Code	Title	Description
1995-11-01	MKLA	Lapsed

Publication	Publication Date	Title
CA1268594A (en)	1990-05-01	Process for the preparation of optically active polyolefins
AU625601B2 (en)	1992-07-16	A supported metallocene-alumoxane catalyst for high pressure polymerization of olefins and a method of preparing and using the same
RU2139291C1 (ru)	1999-10-10	Металлоорганическое соединение
CA2279242C (en)	2006-12-05	New homogeneous olefin polymerization catalyst composition
EP0495849B1 (de)	1994-12-21	Olefinpolymerisationskatalysator aus einer trialkylaluminiummischung, kieselsäuregel und metallocen
JP2816469B2 (ja)	1998-10-27	気相重合用メタロセン−アルモキサン担持触媒の製造方法
EP0799250B1 (de)	2001-03-21	Verfahren zur Herstellung von Polyolefinen in Gegenwart von Katalysatorsystemen sowie Katalysatorsysteme, die Azametallocene enthalten
US4769510A (en)	1988-09-06	Process for the preparation of polyolefins
JP4330176B2 (ja)	2009-09-16	メタロセンを主成分とする高活性均一オレフィン重合系
EP0712416B1 (de)	1999-07-21	Komponenten und katalysatoren zur olefinpolymerisation
CA1231701A (en)	1988-01-19	Process and catalyst for producing polyethylene having a broad molecular weight distribution
CA2210730C (en)	2001-09-11	Olefin polymerization
KR100244381B1 (ko)	2000-02-01	α-올레핀 중합체의 제조방법
EP0646137B1 (de)	1996-12-18	Katalysator auf trager fur 1-(co)olefinpolymerisation
US6350829B1 (en)	2002-02-26	Supported catalyst systems
US6469114B1 (en)	2002-10-22	Metallocene compound and polymerization catalyst comprising heterocyclic group
US20010023231A1 (en)	2001-09-20	Components and catalysts for the polymerization of olefins
JPH02503687A (ja)	1990-11-01	シリカゲル担持メタロセンアルモキサン触媒の製法
JPH03100004A (ja)	1991-04-25	ポリオレフィンワックスの製法
WO1992001005A1 (en)	1992-01-23	Metallocene, hydrocarbylaluminum and hydrocarbylboroxine olefin polymerization catalyst
EP0742226B1 (de)	1998-12-02	Verfahren zur Herstellung von Katalysatoren auf Basis von Boranen für die Herstellung von syndiotaktischen vinyl-aromatischen Polymeren
FI119934B (fi)	2009-05-15	Siirtymämetalliyhdiste
JP3459272B2 (ja)	2003-10-20	オレフィンの重合および共重合方法
US5457171A (en)	1995-10-10	Catalyst systems for the polymerization of C2 -C10 -alkenes
EP1037931A1 (de)	2000-09-27	Katalysatorzusammensetzungen mit gesteigertem leistungsvermögen